


Hypotheticals

by NuwandaSnicket



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Friends to Lovers, M/M
Language: English
Status: Completed
Published: 2016-05-08
Updated: 2016-05-08
Packaged: 2018-06-07 06:13:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,625
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6789679
Author URL: https://archiveofourown.org/users/NuwandaSnicket/pseuds/NuwandaSnicket
Summary: <blockquote class="userstuff">
              <p>"Who do you think would top if you and I were gay?"<br/>A secretly pining Dean asks Cas this question, thoroughly unprepared for the resulting events.</p><p>Based off a prompt.</p>
            </blockquote>





	Hypotheticals

[](http://smg.photobucket.com/user/el_snicket/media/hypothetically_zpsjlhvmrry.jpg.html)

 

“Hey, Cas.”

“Mm?” 

Dean fidgeted from where he was laying on his bed. Cas was sitting on the floor, working on his latest sketch. Dean couldn’t see it from where he was, but he knew it was amazing. Everything Castiel drew was amazing. Everything Cas DID was amazing. CAS was amazing. He was amazing, and Dean had been in love with him since they were in elementary school.

He realized that Cas had stopped sketching and was looking up at him, waiting for him to finish his question. He flushed beneath that attention, beneath Cas’ intense blue gaze. “Uh…” Cas waited expectantly. “Quit staring at me, ya freak!” He gave Cas’ head a shove, pushing him around to face the wall as he had been before. Cas just laughed and did as he was told, returning to his sketch.

“Then don’t start questions and not finish them.”

“I can’t help it. It’s hard to concentrate when you’re looking at me.”

“Apologies.” The smile was clear in Cas’ voice as he continued drawing, and it brought a smile to Dean’s face, even as nervous flutters filled him at the thought of what he was going to ask. Finally, he steeled up the courage.

“Who do you think would top if you and I were gay?”

Dead silence fell as Cas even stopped drawing. “…..together?”

The question was so completely CAS that Dean nearly laughed, rolling his eyes. “Yes, Cas, together.”

“Me,” Cas answered calmly. The answer was so immediate that Dean was taken aback. 

“What? Why?”

Castiel carefully erased a pencil line and blew away the eraser shavings. “A multitude of reasons.”

The boy sounded so completely sure of himself. It got right beneath Dean’s collar, irked some part of him. “Yea, well I think I would.”

“Why’s that.” Even Dean’s objection to Cas’ opinion didn’t bother the boy.

“Cuz I’ve got a bigger dick.” Dean didn’t know this for certain, but he WAS well endowed, to the point where he was willing to challenge Cas on the subject.

THAT got Castiel’s attention. The boy looked over his shoulder, those beautiful eyes staring right at Dean, a brow arched. “Do you.”

Dean swallowed with some difficulty. It was always hard for him to concentrate when Cas got that look on his face, that one raised brow that looked as if he was ready to go all dom on someone. Still, he managed a defiant nod. “Yea. I do.”

Cas continued to stare. Somehow Dean managed not to break eye contact. Finally, Cas carefully set aside his sketchbook and pencils and rose to his feet. His hands went to his belt, unfastening it. Dean’s eyes widened, jaw dropping.

“Wh….what are you doing?” He practically squeaked the words.

“I would’ve thought that was obvious,” Cas answered. “There’s only one way to figure this out. Time to compare.”

Dean stared. “……you’re serious.”

Cas held his belt by one end and, with one sharp yank, pulled it free from his belt loops. “Deadly.”

Dean looked up at his best friend, the boy he had loved all his life, and wondered how things had gotten so out of hand so quickly.

 

**~*~**

 

“Who do you think would top if you and I were gay?”

Sam’s head whipped about at the question, not at all positive he’d heard what he thought he’d just heard. And he had heard some damn strange things coming from Dean’s room over the years (plenty that he’d like to forget) but this one….this was beyond anything he had yet experienced.

Carefully, cautiously, he approached the door, nearing it just in time to hear “I’ve got a bigger dick.” Okay, who the hell was Dean in there with, what the fuck was going on, and, the real question, did Sam truly want to know?

The door was open the barest crack. He leaned in closer, just managing to get the tiniest glimpse. Cas. It was Cas. Of course it was. He should have known that. He had always suspected that Dean and Cas were more than friends…..or had the potential to be. The two showed all the signs of two people who were just friends but desperately wanted to be more.

Then Cas was standing and his hands were going to his belt, undoing it. “Time to compare.” Time to compare….compare dicks? Sam’s eyes widened. Oh no. No, no, no. He was not going to be around for this. If the pants were coming off, God knows where it would go from here, and he was definitely NOT going to be around when it happened. 

Grabbing the car keys, he headed straight out the front door. Dean and Cas could have the house all to themselves. Maybe they could actually get their shit together and realize what they meant to each other.

 

**~*~**

 

Dean slowly rose to his feet, his hands moving to his own fly. True, he was damn proud of his own equipment, but there was a difference between that and actually getting naked in front of the boy he loved. And now he was going to see Cas naked. CAS.

He hadn't seen Cas naked since they were kids. True, there was the locker room after gym class, but they didn't get fully naked there, and anyway, it wasn't polite to stare. Still, Dean had caught fleeting glimpses of Cas in his underwear. He knew the other boy was packing south of the border. He just wasn’t sure how it compared to him.

Dean pushed down his boxer briefs and kicked them aside. He kept his eyes averted for a moment, for some reason feeling too shy to look up. When he did, he saw that Cas was the same way, and his cheeks were also flushed. It made Dean feel somewhat better. Then he looked down….and his jaw dropped.

“DAMN.”

Castiel’s eyes flew up to meet his, nervousness overwhelming his face. “What.”

“You…. _fuck_ , man.” And Dean thought HE was well endowed. And really, he was. So what did that make Cas?

Besides nervous, for Dean’s lack of words seemed to be freaking him out. Dean took pity on him, speaking up at last. 

“Dude, you’re fucking hung!” he blurted out, and immediately turned crimson. That was SO not how he wanted to say that.

Cas looked completely taken aback but then smiled a small, pleased smile, cheeks flushing slightly pink. “Thanks?”

“You’re welcome,” Dean muttered, eyes averted to the floor. He was far too embarrassed to meet Castiel’s eyes.

“You know,” Cas said after a moment, “you’re not too bad yourself.”

THAT got Dean’s attention, head snapping up, looking at Cas with wide eyes. It wasn’t so much the words as the way Cas had SAID the words, a soft, flirtatious tone to his voice. “…I…yea?”

Cas nodded, stepping ever so slightly closer. Dean could feel his cock twitch with interest, beginning to harden. “And by ‘not too bad’ I mean ‘pretty damn impressive’.”

“ _Fuck_ ,” Dean breathed, looking deep into Cas’ eyes as he spoke, unable to break that eye contact. This was not at all how he had expected this afternoon to go, but no way was he complaining. Cas didn’t seem to be, either. It was only then that Dean realized that Cas was hard, too. Cas was hard. He wanted Dean. Cas wanted him.

"So." Castiel's voice was soft as he stepped even closer, their proximity making Dean dizzy. "Do you think we can make this hypothetical sex a reality?"

Dean stared into those beautiful blue eyes, the truth and raw desire there. It was too much to handle. His eyes slid shut, breaking that contact, and he swallowed with some difficulty, managing a short, tight nod.

Mere seconds passed before he felt the brush of lips against his. Cas' lips. Cas was kissing him, as soft and gentle as Dean had ever dreamed it would be. It was _perfect_. His hands came up of their own accord and clutched at the other boy, gripping his shoulder, a handful of hair. Cas moaned in response, mouth opening, and Dean took advantage to slip his tongue into Cas' mouth, to taste him.

Both boys were dizzy when they broke apart. "Is that a yes?" Cas asked breathlessly.

Dean only laughed, hands tugging at the bottom of Castiel’s t-shirt. "Take your shirt off."

Grinning, Cas obeyed, pulling his shirt up and off in one smooth motion and tossing it aside, his hands moving to pull at Dean’s shirt. “You, too.” Dean obediently raised his arms, letting Cas strip him. Those graceful artist’s hands were immediately on him, running greedily over every inch of bared flesh. Dean nearly whimpered at the touch. It wasn’t just that it felt good. It was who was touching him. This was Cas. The person who he had dreamed of for so damn long, and Dean finally had him.

Well…..had him to some extent. Dean may love Cas but Cas thought they were just fooling around. Dean shook the thought away. If this was all he could have of Cas, he would take it.

Castiel kissed him, catching him by surprise, and his heart nearly broke at the beauty of the smile Cas flashed his way. “Stop thinking so hard.”

“I’m not,” Dean objected. He retaliated by giving Cas’ lower lip a little nip, loving the little ‘eep’ the action elicited.

Cas just rolled his eyes, but he was smiling. “Fine. Now.” Hand on Dean’s chest, he gave him a gentle shove till the backs of his knees hit the mattress. “On your back.” His smile now had a predatory edge to it, and nervous lust flared low in Dean’s stomach.

“I…..yea.” But two could play at that game. Rather than simply lie down as Cas commanded, Dean turned his back on the boy and crawled onto the mattress, presenting his backside in what he hoped was a becoming angle. If Castiel’s gasp was any indication, it was. 

Dean glanced over his shoulder from where he knelt on all fours, ass invitingly displayed to Cas. The boy was staring with wide eyes, mouth slightly open. Dean lowered his lashes, his smile coy. “See anything you like?”

He got his response in the form of a firm smack to the ass that had him crying out in surprise. “ _Fuck!_ ” He would never have expected Cas to do that. Then a hand was running over his backside, soothing the stinging skin.

“Yes,” Cas answered. “I see a lot that I like.” He paused, still stroking the spot he had smacked. “…. _God_ , you’re gorgeous.”

Dean was grateful that he was facing away from Castiel, for he knew he was blushing bright red. He ignored the comment, merely pressing back into Cas’ touch, silently demanding more. 

Castiel’s hand continued to move, one thumb tracing a line down one of Dean’s cheeks, lower and lower until it suddenly pressed ever so lightly against that puckered entrance. Dean jolted at the touch.

“ _Fuck!_ ”

Cas chuckled, the noise rolling low and deep in his chest and Goddammit it was sexy. “Got any lube?” His thumb continued to move, stroking teasing circles over Dean’s perineum. It was hard to concentrate, but somehow Dean managed to get a coherent thought out. 

“There.” He flailed an arm in the direction of his desk. “Top left drawer.”

Cas’ hand disappeared and Dean whimpered at the loss of it. Cas only chuckled at that and Dean nearly groaned. That noise. That noise shouldn’t be legal.

But Cas returned quickly with the bottle and a condom, and his hand was running over Dean’s skin again. “On your back.”

Dean obeyed without question, turning over and spreading his legs without waiting for instructions. He was glad he did, too, for at the action, something darkened in Castiel’s eyes, something primal and needy. The boy leaned in, pressing kisses to Dean’s inner thigh. “You ever done this before?”

Dean shook his head. “No.” That seemed to surprise Castiel, but he wasn’t able to suppress a smile. He looked….pleased.

“Really?” Cas held up the near empty bottle. “Seem to use a lot of this.”

Dean flushed crimson but refused to answer, thinking how most of that lube was used when he was home alone, slick fingers pressed up his ass as he desperately stroked his cock and moaned Castiel’s name. But there was not a chance in hell he was telling Cas that. “You gonna fuck me or not?”

He half expected Cas to tease him yet again but instead a flush rose in those cheeks and then Cas was surging forwards for another kiss. “Yeah,” Cas answered breathlessly, popping open the bottle and slicking his fingers. “I’m gonna fuck you.”

The first press of Castiel’s fingers was so foreign. Dean had never done this with another person, and he had certainly never expected to do it with Cas. But it was definitely welcome. He sighed happily and relaxed into the feeling, letting his legs fall wider apart. Cas, on the other hand, was tense as a bowstring, watching Dean like a hawk for any sign of discomfort, and he was moving at a snail’s pace.

“Cas, you don’t have to go so slow,” Dean said at last, some amusement in his voice. “I’m not gonna break.”

“Shut up. I know that.”

Dean fought to stifle a laugh. It was clear that Cas had never done this before. That made him ridiculously happy, being Cas' first time. Still, this was taking too long. He reached between them for Castiel’s hand. Cas jumped, surprised.

“What’re you doing??”

“Just relax.” And carefully, he guided Cas’ hand, the two fingers. In, out, in, out. The faster rhythm felt so good and he let out a hiss. “Oh, _fuck_.” He was vaguely aware of Cas staring down at him with flushed cheeks, mouth open. “One more, Cas.” He could feel Cas ever so gently press one more finger into him, and he arched at the sensation. _Fuck_ , it felt so good. Cas could get the angle much better than he could by himself. “Fuck, keep going. Don’t stop.”

Cas didn’t move for a minute, too captivated by Dean. Finally shaking himself from his trance, he continued fucking his fingers into Dean. He had it now, the speed, the stretch, and it was so Goddamn GOOD. Then he hit that sweet spot and Dean couldn’t help it, he gasped out “ _oh!_ ” 

Cas immediately stopped, face terrified. “Are you okay? What did I do?”

Dean wanted both to growl in frustration and yet to laugh. He pulled Cas into a kiss. “You can’t tell me you’ve gotten this far in life and don’t know what a prostate is.”

“OH.” Cas blushed. “Shut up.” In retaliation, he pressed on that spot again, making Dean yelp.

“Oh my God fuck, fuck, okay _fuck_ , fuck me.”

It was clear the effect the words had on Cas, the way Dean was clinging to him. He ran a hand through Dean’s hair, down his cheek, and gave him a gentle kiss. “Lie back, baby,” he said softly.

The words stabbed through Dean like a knife. Baby. Cas had called him “baby”. Almost as if they were truly in a relationship. He pushed the thoughts from his head. Time to center himself in the here and now. Here, in Castiel’s arms. Now, when Cas was his.

Cas finished rolling on a condom and nudged Dean’s legs just wide enough to settle himself between them, leaning in to cup the man’s face, thumb gently stroking his cheek. “Last chance to back out.”

Dean shook his head. “Never.”

Castiel’s answering smile was beautiful. Dean took a deep breath as he felt the first press of Cas’ cock against his entrance, the tight stretch as he was breached. It hurt, it did. But it wasn’t a _bad_ hurt. It was the kind of hurt where you could tell something wonderful was going to come of it. And honestly how could he even really feel it when Cas was there, looking down at him with that soft smile?

Dean bit his lip at a particularly rough twinge of pain, and immediately Cas was cupping his cheek. 

“Are you okay?” Cas’ blue eyes were filled with concern. Dean nodded.

“M’fine.” He leaned up for a kiss. “Don’t stop.”

Cas went slow, but soon he was fully seated inside Dean. Dean almost couldn’t believe it. Cas was _inside_ him. _Fuck_. He wrapped his arms around the boy’s neck, unable to help nuzzling into his throat, loving the resounding chuckle he got in response.

“You good?”

Dean nodded, pulling back to steal a kiss. “I’m good. You?”

Cas shifted his hips experimentally and bit back a little noise at the wave of pleasure that came over him. “Haa….yeah. I’m good.”

“Good.” Dean wrapped his legs around Castiel’s waist, pulling him closer, and smiled up at the other man. “Then fuck me.”

The words went straight to Cas’ groin and he couldn’t have stopped himself had he wanted to. His hips snapped forwards. The gasping moan that the action pulled from Dean was positively sinful. The boy’s head tipped back, exposing the long column of his throat, and Cas couldn’t resist, his mouth latching onto all that bare skin. Dean whimpered, his hands coming up to fist in Cas’ messy brown hair.

“ _Fuck_ , Cas.” His voice was already breathy and Cas had barely done anything. He rolled his hips again, setting up a steady rhythm. He had never fucked another man, didn’t have anything but instinct going for him, but as long as Dean enjoyed it….well, that was all that mattered. And that spot…..if he could find Dean’s prostate, that would be even better. Cas shifted, trying to get Dean into a better position. He slipped an arm beneath Dean’s leg, tugging it higher up.

Dean could definitely get behind this. He let Cas maneuver him, shifting his leg higher and slipping it over Cas’ shoulder. He actually heard Cas gasp a little at that and he looked inquisitively up at him. But he didn’t get much of a chance before Cas was kissing him hard and deep.

“FUCK, you’re bendy.”

Dean laughed breathlessly. “Guess so.” He grinned. “You like that? Thinkin’ bout all the other crazy positions you could fold me into?”

Cas moaned. “ _Fuck_ , Dean, don’t do this to me.”

“Bend me over wherever and however you want, whenever you want?” The idea sounded damn good to Dean, and unbeknownst to him, to Castiel as well. 

Cas growled, hand gripping Dean’s hip possessively. “Yes. I want that.”

“Fuck me hard?” Dean could barely get the words out, he was so far gone. Cas was beautiful, and fucking him within an inch of his life. And oh shit, now Cas’ hand was moving, taking Dean’s cock in hand and jerking him in time with his thrusts.

“Yes,” Cas answered, voice low and fierce. “Fuck you so hard you won’t remember your own name. Fuck you so good you’ll never want _anyone else **ever. Again**_.”

If only Cas knew that Dean already wanted no one else but him. Dean whimpered desperately, Cas’ words and touch overwhelming. Then Cas found it, that angle, hitting his prostate, and Dean came with a cry, his hands clutching at Castiel’s shoulders. 

He was going to say it. Fuck, Dean was going to say “I love you.” He crashed his mouth against Cas’ in a messy, fumbling kiss, managing to muffle the words, instead moaning into Cas’ mouth. It all seemed to do something for Cas, who was coming as well, nipping at Dean’s mouth.

They were silent for several moments, simply holding each other close, foreheads together as they struggled to catch their breath. Castiel was cupping Dean’s face, fingers tracing his skin as though he were something precious, beautiful. Dean was still clinging to Cas as if he were the only thing keeping Dean from breaking apart.

And then their eyes met, and the spell was broken.

The two men looked away from each other with an awkward laugh, flopping back onto the mattress. How to go from being friends to all that had just happened and back to just friends? 

“…..well,” Dean said at last.

Cas just snorted. Dean looked defensively at him. “What.”

“You’re going to make this weird. Don’t make it weird.”

“It IS weird!” Dean protested. All he wanted to do was curl up in Cas’ arms and have everything go right back to how it had been five minutes ago.

“Yeah, but we knew it would be when we started.” Cas hated putting on this air of bravado. Going along with this had been dumb. Having one little taste of Dean was worse than never having him at all, he was sure of it now.

“Yea, I guess,” Dean admitted reluctantly.

“Yeah. C’mere.” Cas grabbed Dean and hauled him closer, an arm around Dean’s shoulders as he held him close. 

Dean had jumped a little in surprise, but he had no qualms about snuggling right up to Cas. “And you don’t think THIS is weird?”

Cas shrugged. “Maybe. But we used to share a bed before this. So I think once we have sex we’re entitled to jump to the next level and cuddle.”

Dean snorted. “Oh, okay then. If that’s how it works.”

“It is.” Cas smiled as Dean snuggled even closer, wrapping his arms around Cas and laying his head on Cas’ chest. They lay like that in silence, content to cuddle and enjoy one another’s presence. But Cas couldn’t help but poke at the issue. "You know, you're pretty hung yourself."

Dean couldn't help a laugh, even as the words sent a little jolt of happiness through him. "Oh I am, am I."

Cas nodded. "Oh, yeah. I'd love to get that thing in me."

This time the words filled Dean with an unmistakable sensation of lust. "Is that so?" he managed.

"Yeah." Cas ran his fingers through Dean's hair, kissed him on the forehead. "Maybe next time." The words were carefully nonchalant but the depth of feeling behind them was unmistakable. Dean shot up, staring at Cas in surprise.

"I.....you.....next time?"

Cas nodded, a small smile on his face. "Next time," he repeated, and it was clear that he was talking about more than just once. He was speaking of an ongoing relationship. Whether this could evolve into something emotional as well as physical, Dean didn’t know, but he would take it. He would take it and he would make it work, make it a real relationship. Somehow, he would make Castiel love him. 

"Hmm," he hummed, pretending to consider the matter. Then he leaned in close, voice a soft murmur as he brushed his lips against Cas' in a gentle kiss. "I think I can handle that."

 

**~two months later~**

 

Dean rolled over beneath the covers. The last two months had been amazing. Being with Cas, able to hold him close, to touch him and kiss him….to make love to him…..that was more than Dean had ever thought he could have. But he still wanted more. Selfish or not, he wanted more. Simply being with Castiel physically wasn’t enough. He wanted all of Cas. He loved Cas, and he wanted Cas to love him back. If he couldn’t have that….well, then, he didn’t want the sex, either.

Dean felt Castiel’s hand in his hair, the touch gentle. “What’re you thinking about,” Cas asked softly.

Dean bit his lip. He had to get it over with. Today when they had made love, he had made certain to focus on every little detail: how Cas felt inside him, wrapped around him…the way those blue eyes never broke eye contact, smiling down at Dean as though he were the only thing that mattered in the entire world.

Yes, Dean had had his last taste of what it was like to be with Cas. Now it was time to nut up and tell Cas the truth. With a sigh, he sat up. “Cas…..I need to tell you something.”

He could feel the nerves that immediately overwhelmed Cas. The boy sat up, looking at Dean with worried eyes. “Is everything okay?”

“Yea. I mean, no. I mean, it is, but….” Dean sighed. “I can’t do this anymore, Cas.”

Cas was hurt. He was trying not to show it, but he was….Dean knew him well enough to tell. “How come?”

“It’s not you, Cas, it’s me.” Dean winced, realizing too late how lame that sounded. Cas obviously did, too, for he laughed harshly.

“Really, Dean? That’s the oldest excuse in the book.”

“I’m serious, Cas. I just…..I can’t keep having this no-strings-attached relationship with you when---“ he broke off, turning away. There was silence as Cas waited, as Dean tried to find his courage.

“When what, Dean?”

_Oh, well,_ he thought, dully. _Here goes everything. Goodbye, Cas._ "When I love you." He could hear the sharp intake of breath and something in his stomach clenched. Somehow he forced himself to meet those blue eyes, so wide with shock. "I'm not going to apologize," he said fiercely, "because I'm not sorry." But before he could continue Cas was taking Dean's face in his hands and covering his mouth with his own, thoroughly silencing him as he kissed the boy within an inch of his life.

Dean let out a startled "mmph!", too surprised to do anything but sit there and let Castiel kiss him. At last the boy pulled away, leaving Dean speechless.

"You _idiot_ ," Cas said breathlessly. "You beautiful, wonderful idiot."

Dean bristled, then the words "beautiful" and "wonderful" registered. "I.....what?"

Castiel ran his fingers through Dean's hair, the feeling so good that Dean nearly arched into it, like a cat. "I love you, too."

It took a moment before the words sank in. Then Dean was filled with the most delicious happiness he had ever known, flooding every inch of his body. He rolled them over, pressing Cas into the mattress and kissing him for everything he was worth.

Cas laughed into the kiss, slipping a leg around Dean’s waist so he could pull their bodies even more flush together. 

“I love you,” Dean mumbled in between kisses. “I love you so much.”

Cas stroked Dean’s cheek, ran his thumb along Dean’s plump lower lip. “I love you, too. More than I can ever say.”

Dean caught Cas’ thumb between his teeth, nipping gently and eliciting a laugh. He smiled down at the other boy. “Does this mean you’re my boyyyyyfriend?” He stretched the word out almost teasingly, but there was a shyness to it. 

Cas leaned upward to steal another kiss. “If you’ll have me,” he answered. Dean thought he would burst from so much happiness. He kissed Cas again, gently tugging a lock of that messy brown hair.

“Always.”

There came a sudden knocking at the door, startling both men. “Guys?” It was Sam. He sounded wary, no doubt hesitant about walking in on something he didn’t want to see. “Are you guys done yet?”

Dean looked from the door to Cas and smiled. "Better go back outside, Sammy," he called over his shoulder. "We're gonna be a while yet."

There came a muffled groan and the sound of feet stomping down the hallway, the front door slamming as Sam left yet again. Cas arched a brow up at Dean. "A while, huh."

Dean just grinned. "Oh yea. We've got a lot of lost time to make up for…..boyfriend." There was something so very happy in that smile, and Cas couldn't help but smile back.

"Well, then." He reached out, cupping Dean's cheek. "We'd better get to it."

 

**~fin~**


End file.
